Daniil Medvedev defeated Denis Shapovalov 6-3 6-3 in the Tokyo semi-final on hard. The result followed the form book — Daniil Medvedev came in ranked #8, leading the head-to-head 3–2, defending last year's round of 32. Daniil Medvedev extended the head-to-head to 4–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2022-10-24 | Vienna | F | hard | Daniil Medvedev | 4-6 6-3 6-2 |
| 2022-08-15 | Cincinnati Masters | R16 | hard | Daniil Medvedev | 7-5 7-5 |
| 2021-09-24 | Laver Cup | RR | hard | Daniil Medvedev | 6-4 6-0 |
| 2018-07-30 | Washington | R32 | hard | Denis Shapovalov | 3-6 6-1 6-4 |
| 2017-08-28 | US Open | R128 | hard | Denis Shapovalov | 7-5 6-1 6-2 |
Averages from each player's recent completed matches (19 vs 20). ATP, WTA & Challenger.